Methyl acetoacetate → 2-Cyclohexyl-5-methyl-2,4-dihydro-pyrazol-3-one

HRID 2218965Notes

Reaction equation

HRID 2218965 reaction equation
Cl.[CH:2]1([NH:8][NH2:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:10](OC)(=[O:15])[CH2:11][C:12]([CH3:14])=O>C(O)(=O)C>[CH:2]1([N:8]2[C:10](=[O:15])[CH2:11][C:12]([CH3:14])=[N:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 207836Cyclohexylhydrazine hydrochloride

Product 1

HCID 101926052-Cyclohexyl-5-methyl-2,4-dihydro-pyrazol-3-oneYield 102.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Cyclohexylhydrazine hydrochloride (2.00 g, 13.3 mmol) and methyl acetoacetate (2.37 g, 20.4 mmol) were combined in glacial acetic acid (55 mL). The reaction was heated to 100° C. for 18 h. After allowing the reaction to cool to RT, the solvent was removed under reduced pressure to give 2.46 g of the desired product as a pale orange solid. This material was used without further purification. MS (ES+) m/z 181.2 (M+H+).

Workup

  1. customthe reaction
  2. temperatureto cool to RT
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9214b6ecbdb94db0820cfd840c644f70
Source dataset
uspto-grants-2008_08
Patent number
US07414040B2

Reaction notes

Loading…